1. Field of the Invention
The cephalosporins of the present invention possess the usual attributes of such compounds and are particularly useful in the treatment of bacterial infections by parenteral administration.
2. Description of the Prior Art
The cephalosporins are a well-known group of semisynthetic antibacterial agents made originally, for example, by acylation of the 7-amino group of the nucleus 7-aminocephalosporanic acid (7-ACA) and later by similar acylation of nuclei derived therefrom, as by modification of its substituent at the 3-position. Various reviews have appeared in the scientific literature (e.g. Cephalosporins and Penicllins - Chemistry and Biology, edited by Edwin H. Flynn, Academic Press, New York, 1972, and particularly pages 554-569) and in the patent literature, e.g. as in U.S. Pat. Nos. 3,687,948, 3,741,965, 3,759,904 and 3,759,905 (all U.S. Class 260-243C).
Issued patents on 3-thiolated cephalosporins in which the 7-substituent is
A. .alpha.-Amino-.alpha.-phenylacetamido include U.S. Pat. Nos. 3,641,021, 3,734,907, 3,687,948, 3,741,965, 3,757,015, 3,743,644, Japan 71/24400 (Farmdoc 46374S), Belgium 776,222 (Farmdoc 38983T; U.K. 1,328,340 which includes various substituents on the benzene ring), Belgium 772,592 (Farmdoc 19696T; U.S. Pat. Nos. 3,687,948, 3,734,907 and 3,757,012), West Germany 2,202,274 (Farmdoc 50428T) corresponding to U.S. Pat. No. 3,759,904, Netherlands 7205644 (Farmdoc 76309T; U.S. Pat. No. 3,757,014); and
B. O-, M- OR P-AMINOETHOXYPHENYLACETAMIDO AS Netherlands 72/13968 (Farmdoc 24740U) corresponding to U.S. Pat. No. 3,759,905 and
C. O-AMINOMETHYLPHENYLACETAMIDO AS Netherlands 72/06326 (Farmdoc 76374T) (which also reviews the older patent literature concerning substituted 7-phenylacetamidocephalosporanic acids) corresponding to U.S. Pat. Nos. 3,766,176 and 3,766,175; and
D. N-(phenylacetimidoyl)aminoacetamido as U.S. Pat. No. 3,692,779; and
E. .alpha.-AMINO-.alpha.-(1,4-CYCLOHEXADIENYL)ACETAMIDO AS IN Belgium 776,222 (Farmdoc 38983T; U.K. 1,328,340).
Additional similar disclosures are found in U.S. Pat. No. 3,692,779 (Belgium 771,189; Farmdoc 12,819T), Japan 72/05550 (Farmdoc 12,921T), Japan 72/05551 (Farmdoc 12,922T), U.S. Pat. No. 3,719,673 (Belgium 759,570; Farmdoc 39819S), Belgium 793,311 (Farmdoc 39702U) and Belgium 793,191 (Farmdoc 39684U).
Issued patents containing a partially hydrogenated benzene ring in the 7-substituent but lacking a thiomethyl group at the 3-position include those in which the 7-substituent is
a. 2-(1,4-cyclohexadien-1-yl)acetamido as in U.S. Pat. No. 3,704,297 (Farmdoc 78154T) and Belgium 759,326 (Farmdoc 38,172S); and
b. .alpha.-amino-.alpha.-(1,4-cyclohexadienyl)acetamido and related compounds as in U.S. Pat. No. 3,485,819; West Germany 2,152,745 (Farmdoc 29606T); and
c. .alpha.-amino-.alpha.-(1,2-cyclohexenyl)acetamido as in Belgium 773,773 (Farmdoc 25515T) and, with a fully unsaturated benzene ring.
d. p-(.alpha.-aminoalkyl)phenylacetamido as in U.S. Pat. No. 3,382,241; and
e. o-aminomethylphenylthioacetamido as in U.S. Pat. No. 3,657,232.